Planning has become complicated for me and I could use some help. Single older women traveling alone through Tuscany in the fall of 2023. I already have a VRBO for 4 weeks in Florence and would like to make day trips from there to Lucca, Pisa, Pistora, Fiesole and Montelupo Florentio.
If I arrive in Rome and train to Orvieto, I would spend 2 nights there and then rent a car. (Would it be better if I wait to visit Orvieto for another time when I can do Assisi as well? If so then I would go to Chiusi to rent a car.)
From there I am going to Montepulciano and spend 2 days driving and exploring the Val D'Orcia region.
From there, driving the Crete Sensei drive on the way to San Gimingiano for 2 nights with one day going to Voltera and evenings in San Giimingiano.
From there I will drive through the Chianti region on the way to Siena where I will drop off the car and stay for 3 days.
From there, train to Florence.
I am looking for relaxed drives with beautiful views I can stop and marvel at and quiet towns before hitting the big city. I would like to spend at most 10 days prior to going to Florence.
Does this route look reasonable? Am I repeating too many views or towns. Would I be better off spending more time in one place and less in another? Am I missing any places? Would it be better to save Orvieto for when I go to Rome as a day trip from there in the future.
Any advice would be appreciated.
Posted by
San Francisco Bay Area (USA)
15161 posts
The only rental company in Orvieto is Hertz. If you need a car with automatic transmission you are more likely to find one in Rome. The drive from Rome to Orvieto is just over an hour, practically all freeway. If you stay in Montepulciano/Pienza area, I recommend more than just 2 nights. There are many places and towns in that area, including the Crete Senesi that you can easily visit from Montepulciano. I would stay at the very least 3, or better, 4 nights. Places to visit are: Montepulciano, Pienza, Monticchiello, Bagno Vignoni, Montalcino, Buonconvento, San Galgano Abbey, San Quirico D’Orcia, Crete Senesi.
From the San Gimignano area you can easily visit various places (besides San Gimignano) like Chianti area, Monteriggioni, Volterra, Certaldo, Colle Val D’Elsa, Barberino Val D’Elsa. If you stay only 2 nights you will basically have only one full day and you won’t be able to visit all that. San Gimignano will need at least half a day, and going to Volterra will involve some driving. You need at least 3 full days (4 nights) to enjoy all of those locations.
To see Siena itself, you need a full day. So at least 2 nights is adequate. 3 nights will give you plenty of time to enjoy it without rushing.
From Siena to Florence the fastest option is the bus. The bus also departs from Via Tozzi, on top of the hill downtown. The train takes longer and the Siena station is outside the city center at the bottom of the hill.
Posted by
11156 posts
Drive on SR 222 , the Chiantigiana, the historic road from Siena to Florence.
You can visit the pretty villages and towns along this route: some of them are Gaiole, Radda, Castellina, Panzano, Greve.
Posted by
OP
DURHAM, NC
55 posts
Thanks Roberto and Suki. Exactly what I was looking for. A great list of small towns that aren't in the travel books. I think I like your time line as well.
Is it reasonable to leave San Gimingiano in the morning and go to the Chianti region? If I start at Greve and take S222 down to Siena, stopping at the small towns in Chianti? Then I can then drop the car off In Sienna.